CN103549635B - Preparation method of resistant starch nutritional carrier based on metal-organic framework as well as product thereof - Google Patents
Preparation method of resistant starch nutritional carrier based on metal-organic framework as well as product thereof Download PDFInfo
- Publication number
- CN103549635B CN103549635B CN201310532919.0A CN201310532919A CN103549635B CN 103549635 B CN103549635 B CN 103549635B CN 201310532919 A CN201310532919 A CN 201310532919A CN 103549635 B CN103549635 B CN 103549635B
- Authority
- CN
- China
- Prior art keywords
- resistant starch
- organic framework
- preparation
- metal
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention discloses a preparation method of a resistant starch nutritional carrier based on a metal-organic framework as well as a product thereof. The preparation method of the resistant starch nutritional carrier comprises the step of adsorbing metal-organic framework structured gamma-cyclodextrin on the surface of octenyl succinic anhydride modified starch (OSA-S) by taking the OSA-S prepared by performing esterification on octenyl succinic anhydride and resistant starch as a base material and under the effects of hydrogen bond, electrostatic force and the like, thus constructing the nutritional carrier with a porous network structure. The nutritional carrier has favorable solution self-aggregation performance; by virtue of the great load quantity of the relatively single OSA-S and the metal-organic framework structured gamma-cyclodextrin, functional substances such as nutritional elements can be embedded in a solid state mode, so that the damage caused by light irradiation, oxygen as well as acid-base and the like is prevented effectively, and a certain slow-release effect is achieved; the resistant starch also has a good health protection effect, and thus the nutritional carrier is expected to be a safe functional food additive applied to the food processing field.
Description
Technical field
The invention belongs to chemistry and food processing technology field, relate to a kind of preparation method of food-grade nutrition carrier, and the product adopting the method obtained.
Background technology
Resistant starch (resistant starch, RS), also known as enzyme resistant starch and indigestibility starch, can not be digested and assimilated by small intestine, and generates SCFA through fermentable in colon.These SCFAs enter blood by colon wall absorption and provide energy, can also reduce pH in intestines, promote the absorption of the micronutrients such as mineral matter.Resistant starch is slow owing to digesting and assimilating, and can delay postprandial blood sugar and rise, and be not easy hunger after eating, and contributes to controlling blood glucose balance, special suitable for patients with diabetes mellitus.In addition, resistant starch also has and improves constipation, reduces the health-care effect such as serum cholesterol, prevention and cure of cardiovascular disease, lowering blood-fat and reducing weight.
Starch octenyl succinate anhydride (Octenyl Succinic Anhydride Modified Starch, OSA-S) be the converted starch obtained through esterification with starch by octenyl succinic acid anhydride (OSA), it has hydrophilic hydroxy-acid group and hydrophobic long alkyl chain, compared with raw starch, there is parents' character of hydrophilic and oleophilic, can be used as emulsion stabilizer, microcapsule wall material etc., is the focus of converted starch research and development both at home and abroad in recent years.China ratified it in 1997 and uses as food additives, and calendar year 2001 expands again its scope of application in food, and its consumption can add according to demand, without the need to controlling.Have not yet to see and octenyl succinic acid anhydride and resistant starch are obtained ocentyl succinic resistant starch ester and the bibliographical information studied its function through esterification.
Metallic organic framework (Metal-organic framework, MOFs) material is the crystalline material with periodically infinite network structure formed by metal ion or metal cluster and organic ligand self assembly, it has the feature such as hybrid inorganic-organic characteristic, structural order and Scalability, microporosity, special photoelectromagnetic character, has been widely used in gas storage and has been separated at present, the field such as medicament slow release and catalysis.There are some researches show, utilize the feature of gamma-cyclodextrin (γ-CD) structure height symmetry, itself and potassium chloride or Potassium Benzoate are reacted, a kind of novel metal organic framework material can be prepared, its safety non-toxic edible, can be used for food industry and field of medical technology.
Up to now, the research that there is not yet based on ocentyl succinic resistant starch ester and metal-organic framework materials structuring food prods level nutrition carrier is reported.
Summary of the invention
In view of this, the object of the invention is to utilize ocentyl succinic resistant starch ester and metal-organic framework materials to build a kind of food-grade nutrition carrier, preparation method is simple, gained carrier has good solution self aggregation performance, more single ocentyl succinic resistant starch ester and the higher load capacity of metal-organic framework materials, the functional mass such as nutrient can be embedded wherein in solid form, effectively avoid that illumination is penetrated, the destruction of oxygen, soda acid etc., play certain slow release effect, resistant starch itself also has good health-care effect simultaneously.
For achieving the above object, after deliberation, the invention provides following technical scheme:
1., based on the preparation method of the resistant starch nutrition carrier of metallic organic framework, comprise the following steps:
A. the preparation of ocentyl succinic resistant starch ester (OSA-RS): be that 1.5-2g:1mL stirs and evenly mixs and makes resistant starch fully swelling by rate of charge by resistant starch and absolute ethyl alcohol, add the ethanol solution of 0.5-2g/mL octenyl succinic acid anhydride more under agitation, the weight ratio of resistant starch and octenyl succinic acid anhydride is 1-4.5:1, regulate pH to 9.0-10.5,90-100 DEG C of heating in water bath for reaction 3-8 hour; After reaction terminates, regulate pH to neutral, filter, Washing of Filter Cake, drying, pulverizing, obtained ocentyl succinic resistant starch ester;
B. the preparation of metal-organic framework materials: be that 1:1-1.5 is soluble in water in molar ratio by gamma-cyclodextrin and Potassium Benzoate, cross and filter insoluble matter, be that 1:1-2.5 adds methyl alcohol by the volume ratio of water and methyl alcohol, mixing, logical nitrogen bubble makes first alcohol and water naturally volatilize, crystallization, filter, washing, dry, obtained metal-organic framework materials;
C. based on the preparation of the resistant starch nutrition carrier of metallic organic framework: the metal-organic framework materials that ocentyl succinic resistant starch ester steps A obtained and step B obtain is in molar ratio for 6-10:1 is soluble in water, abundant vibration makes the two self aggregation form micella, ultrasonic disperse again, filter, drying, obtains the resistant starch nutrition carrier based on metallic organic framework.
Preferably, described steps A is that 1.5g:1mL stirs and evenly mixs and makes resistant starch fully swelling by resistant starch and absolute ethyl alcohol by rate of charge, drip the ethanol solution of 2g/mL octenyl succinic acid anhydride more under agitation, the weight ratio of resistant starch and octenyl succinic acid anhydride is 1:1, pH to 9.5 is regulated, 100 DEG C of heating in water bath for reaction 3 hours with 0.5mol/L sodium hydroxide solution; After reaction terminates, with 0.5mol/L hydrochloric acid solution adjustment pH to neutral, filter, filter cake absolute ethanol washing, less than 50 DEG C dry, pulverizing, obtained ocentyl succinic resistant starch ester.
Preferably, described step B is in molar ratio for 1:1.1 is soluble in water by gamma-cyclodextrin and Potassium Benzoate, removing insoluble matter by filtered through gauze, is that 1:2 adds methyl alcohol by the volume ratio of water and methyl alcohol, mixing, logical nitrogen bubble makes first alcohol and water naturally volatilize, crystallization, by filtered through gauze, crystallization absolute methanol washs, natural air drying, obtained metal-organic framework materials.
Preferably, described step C is that the obtained metal-organic framework materials of the ocentyl succinic resistant starch ester that steps A obtained and step B is in molar ratio for 8:1 is soluble in water, abundant vibration makes the two self aggregation form micella, the ultrasonic process of batch (-type) makes dispersion again, often ultrasonic 5 seconds stop 3 seconds, 400 mesh filter screens filter, spraying dry, the obtained resistant starch nutrition carrier based on metallic organic framework.
2. adopt the resistant starch nutrition carrier based on metallic organic framework prepared by said method.
Beneficial effect of the present invention is: the present invention with octenyl succinic acid anhydride and resistant starch through the obtained amphiphatic ocentyl succinic resistant starch ester of esterification for base material, by the effect such as hydrogen bond and electrostatic force, the gamma-cyclodextrin of metallo-organic framework is adsorbed on the surface of ocentyl succinic resistant starch ester, construct a kind of nutrition carrier with porous network structure, its powder fenestra particle diameter is 50 ~ 80 μm, and specific area is 3 ~ 6m
2/ g, viscosity is 9-20mpa.s, and better, resistance starch content is more than 85% for ductility and gelatinization degree.Experimental result shows, this nutrition carrier has good solution self aggregation performance, more single ocentyl succinic resistant starch ester and the higher load capacity of metal-organic framework materials, the functional mass such as nutrient can be embedded wherein in solid form, effectively avoid that illumination is penetrated, the destruction of oxygen and soda acid etc., play certain slow release effect, resistant starch itself also has good health-care effect simultaneously, is expected to apply in food processing field as a kind of safe functional food additives.
Accompanying drawing explanation
In order to make object of the present invention, technical scheme and beneficial effect clearly, the invention provides following accompanying drawing and being described:
Fig. 1 is the scanning electron microscope (SEM) photograph of the resistant starch nutrition carrier based on metallic organic framework.
Detailed description of the invention
Below in conjunction with accompanying drawing, the preferred embodiments of the present invention are described in detail.
Embodiment 1, preparation based on the resistant starch nutrition carrier of metallic organic framework
Based on the preparation method of the resistant starch nutrition carrier of metallic organic framework, comprise the following steps:
A. the preparation of ocentyl succinic resistant starch ester: resistant starch 300g and absolute ethyl alcohol 200mL is stirred and evenly mixed in the high-speed mixer of 2000rpm and makes resistant starch fully swelling, drip the ethanol solution 150mL of 2g/mL octenyl succinic acid anhydride more under agitation, pH to 9.5,100 DEG C of heating in water bath for reaction 3h are regulated with 0.5mol/L sodium hydroxide solution; After reaction terminates, regulate pH to neutral with 0.5mol/L hydrochloric acid solution, filter, filter cake absolute ethanol washing, less than 50 DEG C dry, pulverize, obtained ocentyl succinic resistant starch ester;
B. the preparation of metal-organic framework materials: gamma-cyclodextrin 21.3g and Potassium Benzoate 2.9g is dissolved in 150mL water, insoluble matter is removed by filtered through gauze, add methyl alcohol 300mL, mixing, slowly passes into nitrogen bubble and first alcohol and water is volatilized naturally, crystallization under room temperature, by filtered through gauze, crystallization absolute methanol washs, natural air drying, obtained metal-organic framework materials;
C. based on the preparation of the resistant starch nutrition carrier of metallic organic framework: the metal-organic framework materials 0.12mmol that the ocentyl succinic resistant starch ester 1.2mmol and step B steps A obtained obtains is soluble in water, abundant vibration makes the two self aggregation form micella, batch (-type) ultrasonic process 2min (often process 5s and stop 3s) makes dispersion again, 400 mesh filter screens filter, spraying dry, the obtained resistant starch nutrition carrier based on metallic organic framework.
The scanning electron microscope (SEM) photograph of gained nutrition carrier as shown in Figure 1.After measured, its powder fenestra particle diameter is 55 μm, and specific area is 5.8m
2/ g, viscosity is 9.2mpa.s, and resistance starch content is 85.8%.
Embodiment 2, preparation based on the resistant starch nutrition carrier of metallic organic framework
Based on the preparation method of the resistant starch nutrition carrier of metallic organic framework, comprise the following steps:
A. the preparation of ocentyl succinic resistant starch ester: resistant starch 500g and absolute ethyl alcohol 300mL is stirred and evenly mixed in the high-speed mixer of 3000rpm and makes resistant starch fully swelling, drip the ethanol solution 125mL of 0.96g/mL octenyl succinic acid anhydride more under agitation, pH to 10.0,95 DEG C of heating in water bath for reaction 5h are regulated with 0.5mol/L sodium hydroxide solution; After reaction terminates, regulate pH to neutral with 0.5mol/L hydrochloric acid solution, filter, filter cake absolute ethanol washing, less than 50 DEG C dry, pulverize, obtained ocentyl succinic resistant starch ester;
B. the preparation of metal-organic framework materials: gamma-cyclodextrin 30g and Potassium Benzoate 3.7g is dissolved in 230mL water, insoluble matter is removed by filtered through gauze, add methyl alcohol 500mL, mixing, slowly passes into nitrogen bubble and first alcohol and water is volatilized naturally, crystallization under room temperature, by filtered through gauze, crystallization absolute methanol washs, natural air drying, obtained metal-organic framework materials;
C. based on the preparation of the resistant starch nutrition carrier of metallic organic framework: the metal-organic framework materials 0.2mmol that the ocentyl succinic resistant starch ester 1.6mmol and step B steps A obtained obtains is soluble in water, abundant vibration makes the two self aggregation form micella, batch (-type) ultrasonic process 2min (often process 5s and stop 3s) makes dispersion again, 400 mesh filter screens filter, spraying dry, the obtained resistant starch nutrition carrier based on metallic organic framework.
After measured, the powder fenestra particle diameter of gained nutrition carrier is 65 μm, and specific area is 4.2m
2/ g, viscosity is 15.6mpa.s, and resistance starch content is 85.4%.
Embodiment 3, preparation based on the resistant starch nutrition carrier of metallic organic framework
Based on the preparation method of the resistant starch nutrition carrier of metallic organic framework, comprise the following steps:
A. the preparation of ocentyl succinic resistant starch ester: resistant starch 200g and absolute ethyl alcohol 100mL is stirred and evenly mixed in the high-speed mixer of 1500rpm and makes resistant starch fully swelling, drip the ethanol solution 160mL of 0.5g/mL octenyl succinic acid anhydride more under agitation, pH to 10.5,90 DEG C of heating in water bath for reaction 8h are regulated with 0.5mol/L sodium hydroxide solution; After reaction terminates, regulate pH to neutral with 0.5mol/L hydrochloric acid solution, filter, filter cake absolute ethanol washing, less than 50 DEG C dry, pulverize, obtained ocentyl succinic resistant starch ester;
B. the preparation of metal-organic framework materials: gamma-cyclodextrin 10g and Potassium Benzoate 1.24g is dissolved in 130mL water, insoluble matter is removed by filtered through gauze, add methyl alcohol 180mL, mixing, slowly passes into nitrogen bubble and first alcohol and water is volatilized naturally, crystallization under room temperature, by filtered through gauze, crystallization absolute methanol washs, natural air drying, obtained metal-organic framework materials;
C. based on the preparation of the resistant starch nutrition carrier of metallic organic framework: the metal-organic framework materials 0.2mmol that the ocentyl succinic resistant starch ester 1.2mmol and step B steps A obtained obtains is soluble in water, abundant vibration makes the two self aggregation form micella, batch (-type) ultrasonic process 2min (often process 5s and stop 3s) makes dispersion again, 400 mesh filter screens filter, spraying dry, the obtained resistant starch nutrition carrier based on metallic organic framework.
After measured, the powder fenestra particle diameter of gained nutrition carrier is 80 μm, and specific area is 3.4m
2/ g, viscosity is 19.5mpa.s, and resistance starch content is 85.2%.
Embodiment 4, based on the resistant starch nutrition carrier of metallic organic framework to the encapsulating of nutrient
The resistant starch nutrition carrier 0.5g based on metallic organic framework that Example 1,2,3 is obtained respectively, Tween80 and nutrient (vitamin C, forulic acid and curcumin), add absolute ethyl alcohol 2mL, and mixing, obtains mixed liquor, for subsequent use; Under 55 DEG C of heating water baths, stirring condition, fast above-mentioned mixed liquor is injected in 20mL aqueous vehicles and 0.01mol/L PBS (pH 7.4, containing 0.16mol/L NaCl) with syringe, stir aquation 45min, decompression rotary evaporation removing ethanol (55 DEG C, vacuum 0.1MPa), cool rapidly, ice-bath ultrasonic process, 4 DEG C of hold over night, nitrogen-sealed is filled with, obtained encapsulated member after refrigerated centrifuge 30min (4 DEG C, 1.2g).Measure the nutrient total content of encapsulated member and the content of free nutrient, computational envelope rate.The total content of nutrient measures and adopts Tween80 solubilising method: get 0.5g encapsulated member and put in 10mL scale test tube, add the ethanolic solution 1mL of 10% (w/w) Tween80, after whirlpool mixes 30 seconds, 10mL is settled to, with the total content of ultraviolet-visible spectrophotometer or high effective liquid chromatography for measuring nutrient by deionized water.The assay of free nutrient adopts organic solvent washing method: get 0.5g encapsulated member and put in 10mL scale test tube, add pentane 5mL, whirlpool mixes 3 minutes, centrifugal 5 minutes of 2000r/min, collect upper strata pentane liquid, repeat extraction operation once, merge pentane liquid, nitrogen dries up rear ethanol and is settled to 10mL, the content of the nutrient that dissociates with ultraviolet-visible spectrophotometer or high effective liquid chromatography for measuring.Envelop rate computing formula is: envelop rate (%)=100 × (nutrient total content-free nutrient content)/nutrient total content.The ocentyl succinic resistant starch ester that Example 1 is obtained respectively and each 0.5g of metal-organic framework materials, prepare encapsulated member according to above-mentioned same procedure and carry out entrapment efficiency determination.
The results are shown in Table 1, with the resistant starch nutrition carrier based on metallic organic framework for encapsulation vehicle, more single with ocentyl succinic resistant starch ester or metal-organic framework materials for encapsulation vehicle, higher to the envelop rate of nutrient (vitamin C, forulic acid and curcumin), this illustrates that the ocentyl succinic resistant starch ester more single based on the resistant starch nutrition carrier of metallic organic framework that the present invention obtains and metal-organic framework materials have higher load capacity.
Table 1 based on the resistant starch nutrition carrier of metallic organic framework to the envelop rate of nutrient
What finally illustrate is, above preferred embodiment is only in order to illustrate technical scheme of the present invention and unrestricted, although by above preferred embodiment to invention has been detailed description, but those skilled in the art are to be understood that, various change can be made to it in the form and details, and not depart from claims of the present invention limited range.
Claims (5)
1., based on the preparation method of the resistant starch nutrition carrier of metallic organic framework, it is characterized in that, comprise the following steps:
A. the preparation of ocentyl succinic resistant starch ester: be that 1.5-2g:1mL stirs and evenly mixs and makes resistant starch fully swelling by rate of charge by resistant starch and absolute ethyl alcohol, add the ethanol solution of 0.5-2g/mL octenyl succinic acid anhydride more under agitation, the weight ratio of resistant starch and octenyl succinic acid anhydride is 1-4.5:1, regulate pH to 9.0-10.5,90-100 DEG C of heating in water bath for reaction 3-8 hour; After reaction terminates, regulate pH to neutral, filter, Washing of Filter Cake, drying, pulverizing, obtained ocentyl succinic resistant starch ester;
B. the preparation of metal-organic framework materials: be that 1:1-1.5 is soluble in water in molar ratio by gamma-cyclodextrin and Potassium Benzoate, cross and filter insoluble matter, be that 1:1-2.5 adds methyl alcohol by the volume ratio of water and methyl alcohol, mixing, logical nitrogen bubble makes first alcohol and water naturally volatilize, crystallization, filter, washing, dry, obtained metal-organic framework materials;
C. based on the preparation of the resistant starch nutrition carrier of metallic organic framework: the metal-organic framework materials that ocentyl succinic resistant starch ester steps A obtained and step B obtain is in molar ratio for 6-10:1 is soluble in water, abundant vibration makes the two self aggregation form micella, ultrasonic disperse again, filter, drying, obtains the resistant starch nutrition carrier based on metallic organic framework.
2. as claimed in claim 1 based on the preparation method of the resistant starch nutrition carrier of metallic organic framework, it is characterized in that, described steps A is that 1.5g:1mL stirs and evenly mixs and makes resistant starch fully swelling by resistant starch and absolute ethyl alcohol by rate of charge, drip the ethanol solution of 2g/mL octenyl succinic acid anhydride more under agitation, the weight ratio of resistant starch and octenyl succinic acid anhydride is 1:1, pH to 9.5 is regulated, 100 DEG C of heating in water bath for reaction 3 hours with 0.5mol/L sodium hydroxide solution; After reaction terminates, with 0.5mol/L hydrochloric acid solution adjustment pH to neutral, filter, filter cake absolute ethanol washing, less than 50 DEG C dry, pulverizing, obtained ocentyl succinic resistant starch ester.
3. as claimed in claim 1 based on the preparation method of the resistant starch nutrition carrier of metallic organic framework, it is characterized in that, described step B be by gamma-cyclodextrin and Potassium Benzoate in molar ratio for 1:1.1 is soluble in water, remove insoluble matter by filtered through gauze, be that 1:2 adds methyl alcohol by the volume ratio of water and methyl alcohol, mixing, logical nitrogen bubble makes first alcohol and water naturally volatilize, crystallization, by filtered through gauze, crystallization absolute methanol washs, natural air drying, obtained metal-organic framework materials.
4. as claimed in claim 1 based on the preparation method of the resistant starch nutrition carrier of metallic organic framework, it is characterized in that, described step C is that the obtained metal-organic framework materials of the ocentyl succinic resistant starch ester that steps A obtained and step B is in molar ratio for 8:1 is soluble in water, abundant vibration makes the two self aggregation form micella, the ultrasonic process of batch (-type) makes dispersion again, often ultrasonic 5 seconds stop 3 seconds, 400 mesh filter screens filter, spraying dry, the obtained resistant starch nutrition carrier based on metallic organic framework.
5. adopt the resistant starch nutrition carrier based on metallic organic framework that described in any one of Claims 1-4 prepared by method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310532919.0A CN103549635B (en) | 2013-11-01 | 2013-11-01 | Preparation method of resistant starch nutritional carrier based on metal-organic framework as well as product thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310532919.0A CN103549635B (en) | 2013-11-01 | 2013-11-01 | Preparation method of resistant starch nutritional carrier based on metal-organic framework as well as product thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103549635A CN103549635A (en) | 2014-02-05 |
| CN103549635B true CN103549635B (en) | 2015-04-29 |
Family
ID=50004144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310532919.0A Expired - Fee Related CN103549635B (en) | 2013-11-01 | 2013-11-01 | Preparation method of resistant starch nutritional carrier based on metal-organic framework as well as product thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103549635B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107151328B (en) * | 2016-03-04 | 2020-11-06 | 中国科学院上海药物研究所 | Sucralose-loaded cyclodextrin-metal organic framework compound and preparation method thereof |
| CN106520747A (en) * | 2016-09-28 | 2017-03-22 | 广州凯耀资产管理有限公司 | Novel immobilized enzyme preparation, and preparation method and application thereof |
| CN106984276B (en) * | 2017-05-08 | 2019-06-25 | 中国农业科学院蔬菜花卉研究所 | Metal-organic framework material, preparation method and application |
| US20220008561A1 (en) * | 2018-11-13 | 2022-01-13 | Northwestern University | Bismuth metal-organic frameworks for use as x-ray computed tomography contrast agents |
| CN115304782B (en) * | 2022-08-22 | 2023-04-18 | 齐鲁工业大学 | High internal phase Pickering emulsion stabilizer for 3D printing and preparation method and application thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5695803A (en) * | 1995-06-06 | 1997-12-09 | Iowa State University Research Foundation, Inc. | Nutritional products containing modified starches |
| CN1563096A (en) * | 2004-04-07 | 2005-01-12 | 广西百事达淀粉有限公司 | New technique for producing starch of octane succinate |
| CN1903883A (en) * | 2005-07-28 | 2007-01-31 | 四平帝达变性淀粉有限公司 | Predextrinization octeneyl succinate starch and its preparation method |
| CN101215385A (en) * | 2008-01-16 | 2008-07-09 | 西南大学 | Process for preparing nano-starch powder |
| CN101407552A (en) * | 2008-11-27 | 2009-04-15 | 诸城兴贸玉米开发有限公司 | Technique for producing low viscosity octenylsuccinate starch by oxidation process |
| CN101624423A (en) * | 2009-08-03 | 2010-01-13 | 甘肃圣大方舟马铃薯变性淀粉有限公司 | Method for preparing starch octenyl succinate anhydride |
| CN102952198A (en) * | 2011-12-06 | 2013-03-06 | 华中农业大学 | Method for preparing octenyl succinic acid modified starch and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005203317A1 (en) * | 2004-07-29 | 2006-02-16 | Brunob Ii B.V. | Use of a chemically modified starch product |
-
2013
- 2013-11-01 CN CN201310532919.0A patent/CN103549635B/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5695803A (en) * | 1995-06-06 | 1997-12-09 | Iowa State University Research Foundation, Inc. | Nutritional products containing modified starches |
| CN1563096A (en) * | 2004-04-07 | 2005-01-12 | 广西百事达淀粉有限公司 | New technique for producing starch of octane succinate |
| CN1903883A (en) * | 2005-07-28 | 2007-01-31 | 四平帝达变性淀粉有限公司 | Predextrinization octeneyl succinate starch and its preparation method |
| CN101215385A (en) * | 2008-01-16 | 2008-07-09 | 西南大学 | Process for preparing nano-starch powder |
| CN101407552A (en) * | 2008-11-27 | 2009-04-15 | 诸城兴贸玉米开发有限公司 | Technique for producing low viscosity octenylsuccinate starch by oxidation process |
| CN101624423A (en) * | 2009-08-03 | 2010-01-13 | 甘肃圣大方舟马铃薯变性淀粉有限公司 | Method for preparing starch octenyl succinate anhydride |
| CN102952198A (en) * | 2011-12-06 | 2013-03-06 | 华中农业大学 | Method for preparing octenyl succinic acid modified starch and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103549635A (en) | 2014-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103549635B (en) | Preparation method of resistant starch nutritional carrier based on metal-organic framework as well as product thereof | |
| CN101444495B (en) | Vitamin E microcapsule preparation method | |
| CN101015342A (en) | Preparation method of lycopersicin microcapsule | |
| CN105315508B (en) | A kind of preparation method of modified graphene chitosan laminated film | |
| CN104211819A (en) | Preparation method and modification method of taro starch nanoparticles as well as application of taro starch nanoparticles | |
| CN104003404B (en) | A kind of preparation method and its usage of porous silicon dioxide nano particle | |
| CN112544955B (en) | Food raw material rich in slowly digestible and resistant starch and preparation method and application thereof | |
| CN102919857B (en) | Edible calcium carbonate microspheres and preparation method thereof | |
| CN111096956A (en) | Preparation method of pH response intestinal targeting active factor carrying system based on anionic sodium alginate | |
| CN114656645A (en) | Preparation method of cyclodextrin metal organic framework stably existing in water phase | |
| CN111067096B (en) | Porous starch microcapsule embedding lutein and preparation method thereof | |
| CN104856963A (en) | Astaxanthin-sodium alginate sustained release microspheres as well as preparation method and application thereof | |
| CN107136503A (en) | A kind of method that starch embedding lutein prepares microcapsules | |
| CN113730597A (en) | Micro-nano carrier based on starch-curcumin conjugate and application thereof | |
| Feng et al. | Effect of V-type crystallinity and starch particle structure on the oil loading capacity and anti-oxidation | |
| Zhao et al. | Recent advances of octenyl succinic anhydride modified polysaccharides as wall materials for nano‐encapsulation of hydrophobic bioactive compounds | |
| CN104352442A (en) | Mifepristone chitosan sustained release microspheres and preparation method thereof | |
| CN113150312A (en) | Preparation method and application of acetylated starch nano-micelle | |
| CN105777919B (en) | The efficient stable state preparation method of soybean lecithin | |
| CN101139280A (en) | Sodium acetate anhydrous and preparation method and usage thereof | |
| CN102659980A (en) | Method for preparing double hydrophilic thermo-sensitive polymer nano micelles | |
| CN102772389A (en) | Water-soluble vitamin E soft capsule and preparation method thereof | |
| CN104402705B (en) | Spherical calcium citrate, and preparation method and application thereof | |
| CN107049959B (en) | Preparation method of urushiol-loaded targeted nano ginkgo starch microspheres | |
| CN113367323A (en) | Green preparation method of food-grade multifunctional lignin/silicon dioxide nanoparticle emulsifier |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20150429 Termination date: 20161101 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |